Palladium-Catalyzed Ligand-Free ortho-Deuteration of Aromatic Carboxylic Acids with D₂O

Abstract

A ligand-free, palladium-catalyzed ortho-deuteration of aromatic carboxylic acids was developed using D₂O as the deuterium source. Compared to their meta-substituted analogues, an unusually lower reactivity in para- and ortho-substituted benzoic acids toward hydrogen isotope exchange was observed. Further investigation revealed that the reaction temperature is a critical parameter for the reactivity, and the modified conditions can afford deuterated products with good to excellent deuterium incorporation.

Key words

benzoic acids - heavy water - deuteration - hydrogen isotope exchange - palladium - ligand-free

Publication History

Received: 30 March 2022

Accepted after revision: 23 May 2022

Accepted Manuscript online:
23 May 2022

Article published online:
23 September 2022

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